1-chloro-2,3,3,3-tetrafluoropropene (CF3CF═CHCl, HCFO-1224yd, hereinafter, referred to also as 1224yd) is a compound having a small global warming potential and giving little load to a global environment, which is considered newly useful for the application in a cleaning agent, a refrigerant, a foaming agent, a solvent, and aerosol in place of chlorofluorocarbons such as 3,3-dichloro-1,1,1,2,2-pentafluoropropane (CF3—CF2—CHCl2, HCFC-225ca) and 1,3-dichloro-1,1,2,2,3-pentafluoropropane (CClF2—CF2—CClFH, HCFC-225cb).
In this specification, as for a halogenated hydrocarbon, an abbreviation of a compound is given in a parenthesis after the name of the compound, and in this specification, the abbreviation is used as required instead of the name of the compound.
As 1224yd, there are a Z-isomer and an E-isomer being geometric isomers, which differ in a position of substituents on a double bond. In this specification, when the name of a compound or an abbreviation of a compound is used, it represents at least one kind selected from a Z-isomer and an E-isomer unless otherwise specified, and the name of a compound or an abbreviation of a compound with (E) or (Z) appended thereafter represents an E-isomer or a Z-isomer of the compound. For example, 1224yd(Z) and 1224yd(E) represent a Z-isomer and an E-isomer of 1224yd respectively.
As a production example of 1224yd, Patent Reference 1 (International Publication WO 2011/162341), for example, describes that, at the time of obtaining 2,3,3,3-tetrafluoropropene (CF3CF═CH2, HFO-1234yf) by reducing 1,1-dichloro-2,3,3,3-tetrafluoropropene (CF3CF═CCl2, CFO-1214ya, hereinafter, referred to also as 1214ya) through its reaction with hydrogen in the presence of a palladium catalyst, 1224yd is obtained as an intermediate. In Patent Reference 1, 1224yd obtained as the intermediate in the aforesaid reaction as well as 1214ya is used as a raw material compound of HFO-1234yf.
The Patent Reference 1 describes conditions and means for obtaining HFO-1234yf being a subject substance with a high yield in the method of reducing 1214ya through its reaction with hydrogen, but does not describe a method to efficiently obtain 1224yd which is classified as a by-product. That is, in the method of Patent Reference 1, 1224yd is slightly produced, but this method has a problem that a large amount of HFO-1234yf, which is an over-reduced product for 1224yd, and further 1,1,1,2-tetrafluoropropane (CF3CHFCH3, HFC-254eb), which is a reduced product of HFO-1234yf, are produced as by-products.